Hydrazine hydrate (1:1) → HCID 123881419, compound

Participants

Reaction Steps

To a solution of methyl 2-(4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)phenyl)-6-methyl-5-oxo-3-phenyl-5,6,7,8-tetrahydroquinoline-6-carboxylate (54 mg, 0.10 mmol) in anhydrous ethanol (1300 μL) was added hydrazine monohydrate (8 μL, 0.16 mmol). The reaction mixture was heated to reflux under a nitrogen atmosphere for 5 hours, additional hydrazine monohydrate (40 μL, 0.82 mmol) added, and the mixture heated at reflux for 18 hours. After cooling to room temperature the reaction mixture was concentrated to dryness under reduced pressure, purified by Biotage chromatography (silica, hexane:ethyl acetate, gradient elution from 88:12 to 0:100) to give the desired product as a yellow solid (12 mg, 23% yield). 1H-NMR (500 MHz, CDCl3) δ 8.72 (1H, s), 8.09 (1H, s), 7.34 (2H, d), 7.30 (2H, d), 7.23-7.28 (3H, m), 7.16-7.22 (2H, m), 5.05 (1H, br s), 3.32-3.44 (1H, m), 3.19-3.32 (1H, br m), 2.41-2.60 (4H, br m), 2.26-2.35 (1H, dd), 1.97-2.11 (2H, m), 1.74-1.86 (1H, m), 1.45 (3H, s), 1.14-1.44 (9H, br m). LCMS (Method A) RT=6.60 min, M+H+=523.17.

Provenance & Evidence